# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_SeAN
_database_code_depnum_ccdc_archive 'CCDC 2213389'
loop_
_audit_author_name
_audit_author_address
'Zhiqiang Yang'
;Jilin University
China
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2022-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Selenanthren
_chemical_formula_moiety         'C12 H8 Se2'
_chemical_formula_sum            'C12 H8 Se2'
_chemical_formula_weight         310.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1157(5)
_cell_length_b                   6.2539(3)
_cell_length_c                   14.6000(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.833(2)
_cell_angle_gamma                90
_cell_volume                     1040.63(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      3.58
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.058
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17856
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.767
_diffrn_reflns_theta_min         3.575
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1960
_reflns_number_total             2206
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0107(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+0.5651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0456
_refine_ls_wR_factor_ref         0.0473
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C8(H8), C5(H5), C3(H3), C4(H4), C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.14529(2) 0.42414(4) 0.46301(2) 0.03744(9) Uani 1 1 d . . . . .
Se2 Se 0.26523(2) 0.88028(3) 0.42127(2) 0.04293(9) Uani 1 1 d . . . . .
C1 C 0.14850(18) 0.4906(3) 0.33644(15) 0.0309(4) Uani 1 1 d . . . . .
C12 C 0.3543(2) 0.6829(3) 0.51829(14) 0.0345(5) Uani 1 1 d . . . . .
C7 C 0.30482(19) 0.4934(3) 0.53531(15) 0.0335(5) Uani 1 1 d . . . . .
C6 C 0.19765(19) 0.6811(3) 0.31900(15) 0.0339(5) Uani 1 1 d . . . . .
C2 C 0.0975(2) 0.3489(4) 0.26083(17) 0.0395(5) Uani 1 1 d . . . . .
H2 H 0.067475 0.219323 0.272964 0.047 Uiso 1 1 calc R . . . .
C11 C 0.4695(2) 0.7307(4) 0.57251(16) 0.0433(5) Uani 1 1 d . . . . .
H11 H 0.503050 0.857082 0.560998 0.052 Uiso 1 1 calc R . . . .
C8 C 0.3717(2) 0.3525(4) 0.60609(17) 0.0445(6) Uani 1 1 d . . . . .
H8 H 0.339510 0.223749 0.616720 0.053 Uiso 1 1 calc R . . . .
C5 C 0.1942(2) 0.7278(4) 0.22501(17) 0.0450(6) Uani 1 1 d . . . . .
H5 H 0.228531 0.852776 0.212919 0.054 Uiso 1 1 calc R . . . .
C3 C 0.0917(2) 0.4012(4) 0.16743(18) 0.0506(6) Uani 1 1 d . . . . .
H3 H 0.054907 0.308774 0.116272 0.061 Uiso 1 1 calc R . . . .
C4 C 0.1398(2) 0.5890(5) 0.14940(18) 0.0530(7) Uani 1 1 d . . . . .
H4 H 0.135754 0.622668 0.086299 0.064 Uiso 1 1 calc R . . . .
C10 C 0.5347(2) 0.5916(4) 0.64355(17) 0.0495(6) Uani 1 1 d . . . . .
H10 H 0.611940 0.624677 0.680123 0.059 Uiso 1 1 calc R . . . .
C9 C 0.4856(2) 0.4039(4) 0.66038(18) 0.0505(6) Uani 1 1 d . . . . .
H9 H 0.529662 0.311087 0.708770 0.061 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.907(2) . ?
Se1 C7 1.911(2) . ?
Se2 C12 1.912(2) . ?
Se2 C6 1.903(2) . ?
C1 C6 1.393(3) . ?
C1 C2 1.386(3) . ?
C12 C7 1.388(3) . ?
C12 C11 1.384(3) . ?
C7 C8 1.390(3) . ?
C6 C5 1.390(3) . ?
C2 C3 1.381(3) . ?
C11 C10 1.379(4) . ?
C8 C9 1.376(4) . ?
C5 C4 1.383(4) . ?
C3 C4 1.376(4) . ?
C10 C9 1.375(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 C7 97.84(9) . . ?
C6 Se2 C12 98.22(9) . . ?
C6 C1 Se1 120.91(15) . . ?
C2 C1 Se1 118.83(16) . . ?
C2 C1 C6 120.2(2) . . ?
C7 C12 Se2 120.95(16) . . ?
C11 C12 Se2 119.38(17) . . ?
C11 C12 C7 119.7(2) . . ?
C12 C7 Se1 120.79(16) . . ?
C12 C7 C8 119.8(2) . . ?
C8 C7 Se1 119.45(18) . . ?
C1 C6 Se2 120.87(16) . . ?
C5 C6 Se2 119.85(17) . . ?
C5 C6 C1 119.3(2) . . ?
C3 C2 C1 119.7(2) . . ?
C10 C11 C12 120.2(2) . . ?
C9 C8 C7 119.8(2) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C3 C2 120.5(2) . . ?
C3 C4 C5 120.1(2) . . ?
C9 C10 C11 120.1(2) . . ?
C10 C9 C8 120.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_preparation       Luminescent
